Carbazole-fuorene-triarylamine derivatives for use as materials in organic electroluminescent devices

Abstract

This application relates to a compound represented by one of formulas (1-1) to (1-3), to a method for preparing such a compound, to an electronic device comprising one or more such compounds, and to the use of such compounds in an electronic device.

Description

Technical Field

[0001] The present invention relates to a compound represented by one of formulas 1-1 to 1-3, to a method for preparing such a compound, to an electronic device comprising one or more such compounds, and to the use of such compounds in an electronic device. Background Technology

[0002] In the context of this application, "electronic device" should be understood to refer to so-called organic electronic devices that contain organic semiconductor materials as functional materials. More specifically, these should be understood to refer to OLEDs (Organic Light Emitting Devices). The term OLED should be understood to refer to an electronic device having one or more layers containing organic compounds and emitting light when a voltage is applied. The general principles of the construction and function of OLEDs are known to those skilled in the art.

[0003] There is great interest in improving performance data in electronic devices, especially OLEDs. Currently, no completely satisfactory solution has been found in these areas.

[0004] The light-emitting layer and the hole-transporting layer have a significant impact on the performance data of electronic devices. Novel compounds are being sought for these layers, particularly hole-transporting compounds and compounds that can serve as hole-transporting matrix materials in the light-emitting layer, especially for phosphorescent light-emitting devices. To this end, compounds with high glass transition temperatures, high stability, and high hole conductivity are being sought. High stability of the compounds is a prerequisite for achieving long lifetimes in electronic devices. Furthermore, there is a need to find compounds that, when used in electronic devices, lead to improvements in device performance data, particularly high efficiency, long lifetime, and low operating voltage.

[0005] In the prior art, fluoreneamine is known as a hole transport material and hole transport matrix material for electronic devices. However, there is still room for improvement in the aforementioned properties.

[0006] CN 115109018 A describes a fluorene derivative with two amine groups substituted at the 1 and 4 positions as a hole transport material.

[0007] CN 112679534 A describes a fluorene derivative as an intermediate compound, in which two carbazole groups are substituted at the 1 and 3 positions and an amine is substituted at the 6 position.

[0008] CN 113387818 A describes a fluorene derivative with diamine substitution at the 1,2 positions as an electronic component.

[0009] Aromatic amines of the following formula have been found to have excellent suitability for use in electronic devices, characterized by specific combinations of substituent groups and specific substitution positions on the fluorene ring. They are particularly suitable for use in OLEDs, and even more particularly suitable therein as hole transport materials and as hole transport matrix materials, especially as hole transport matrix materials for phosphorescent emitters. These compounds result in high lifetime, high efficiency, and low operating voltage in the devices. Preferably, the discovered compounds have high glass transition temperatures, high stability, low sublimation temperatures, good solubility, good synthetic accessibility, and high hole conductivity. Summary of the Invention

[0010] Therefore, the present invention first provides a compound, said compound being represented by one of formulas 1-1 to 1-3:

[0011] The groups and markings that appear are as follows: X 11 For CR 11 Or N, X 12 For CR 12 Or N, X 13 For CR 13 Or N, X 14 For CR 14 Or N, X 15 For CR 15 Or N, X 16 For CR 16 Or N, and X 17 For CR 17 Or N; R a and R b Each occurrence represents a group represented by formula 2-1 or 2-2, and satisfies at least one of the following conditions 1-1 and 1-2:

[0012] <Condition 1-1>

[0013] R a Let R be the group represented by formula 2-1, and R b For the group represented by formula 2-2, <Condition 1-2> R a Let R be the group represented by formula 2-2, and R b The group represented by formula 2-1; L 1 and L 2Each occurrence may represent a single key, either identically or differently, or each key may be represented by one or more R keys. 3 Aromatic or heteroaromatic ring systems with 5 to 40 ring atoms that are substituted with functional groups; k1 and k2 each time they appear, they may represent 1, 2, or 3, and where L 1 If it is a single bond, then k1 is 1, if L 2 If it is a single bond, then k2 is 1; Ar 11 Ar 12 Ar 21 and Ar 22 Each occurrence, whether identical or different, represents that each can be represented by one or more groups R. 3 Substituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms; E represents a single bond; R 11 To R 17 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) 4 )2,C(=O)R 4 , P(=O)(R 4 )2,S(=O)R 4 S(=O)2R 4 NO2, Si(R) 4 3, B(OR) 4 )2, OSO2R 4 Each can be generated by one or more groups R 4 The substituted linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or the branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 4 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms can be substituted by one or more R groups. 4 The substituted aryloxy group having 5 to 60 ring atoms, or the group represented by formula 2-2; wherein the group R 11 To R18 The two groups that can form can be formed by one or more groups R 4 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; R 2 and R 3 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 3, B(OR) 5 )2, OSO2R 5 Each can be generated by one or more groups R 5 The substituted linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or the branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 5 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, or substituted aromatic or heteroaromatic ring systems that can be substituted by one or more R groups 5 Substituted aryloxy groups having 5 to 60 ring atoms; wherein group R 2 and R 3 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; R 4 and R 5Each occurrence may represent, in the same or different ways, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R', each of which is a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by R'C=CR', C≡C, ... Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O, S or CONR´ are substituted and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, in each case an aromatic or heteroaromatic ring system having 5 to 60 ring atoms that may be substituted by one or more groups R´, or an aryloxy group having 5 to 60 ring atoms that may be substituted by one or more groups R´, wherein two adjacent substituents R may form a monocyclic or polycyclic aliphatic or aromatic ring system that may be substituted by one or more groups R´; Ar, each time it appears, represents an aromatic or heteroaromatic ring system with 5 to 40 ring atoms that can be substituted by one or more groups R' in each case; R´, each time appearing, represents the same or different H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and one or more H atoms may be replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

[0014] The present invention also provides a method for preparing a compound represented by one of formulas 1-1 to 1-3 as described above or preferred later.

[0015] The present invention also provides a formulation comprising at least one compound represented by one of formulas 1-1 to 1-3 as described above or preferred later, and at least one solvent.

[0016] The present invention also provides an electronic device comprising at least one compound represented by one of formulas 1-1 to 1-3 as described above or preferred later.

[0017] The present invention also provides the use of compounds represented by one of formulas 1-1 to 1-3 as described above or preferred later in electronic devices. Detailed Implementation

[0018] In the context of this invention, "D" or "D atom" refers to deuterium.

[0019] The following definitions apply to chemical groups used as general definitions. They all apply unless further specific definitions are given.

[0020] In the context of this invention, aryl groups contain 6 to 60 ring atoms, preferably carbon atoms. In the context of this invention, heteroaryl groups contain 5 to 60 ring atoms, wherein the ring atoms comprise carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 5. Heteroatoms are preferably selected from N, O, and / or S. Aryl groups or heteroaryl groups are to be understood herein to mean one of the following: a simple aromatic ring derived from benzene, i.e., phenyl; or a simple heteroaryl ring derived, for example, from pyridine, pyrimidine, or thiophene; or a fused aryl or heteroaryl group derived, for example, from naphthalene, anthracene, phenanthrene, quinoline, or isoquinoline. Therefore, aryl groups having 6 to 18 carbon atoms are preferably phenyl, naphthyl, phenanthrene, or biphenylidene, and there is no limitation on the connection of aryl groups as substituents. In the context of this invention, aryl or heteroaryl groups may contain one or more R groups, wherein the substituents R are as described below.

[0021] In the context of this invention, aromatic ring systems contain 6 to 60 ring atoms. Aromatic ring systems also include aryl groups as described above.

[0022] The aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and biphenylene group.

[0023] In the context of this invention, heteroaromatic ring systems contain 5 to 60 ring atoms and at least one heteroatom. Preferred heteroaromatic ring systems have 10 to 40 ring atoms and at least one heteroatom. Heteroaromatic ring systems also include heteroaryl groups as described above. The heteroatom in the heteroaromatic ring system is preferably selected from N, O, and / or S.

[0024] In the context of this invention, aromatic or heteroaromatic ring systems should be understood to refer not only to systems containing only aryl or heteroaromatic groups, but also to systems in which multiple aryl or heteroaromatic groups may be separated by non-aromatic units (preferably less than 10% of non-H atoms) such as carbon, nitrogen, or oxygen atoms or carbonyl groups. For example, systems such as 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, diaryl esters, piracene, etc., should therefore also be considered aromatic or heteroaromatic ring systems in the context of this invention, as should systems in which two or more aryl groups are separated, for example, by straight-chain or cyclic alkyl groups or by silyl groups. Furthermore, systems in which two or more aryl or heteroaromatic groups are directly bonded to each other, such as biphenyl, terphenyl, tetraphenyl, or bipyridine, are also covered by the definition of aromatic or heteroaromatic ring systems.

[0025] Aromatic or heteroaromatic ring systems having 5 to 60 ring atoms and capable of being linked to aromatic or heteroaromatic systems at any desired position should be understood to refer to groups derived, for example, from the following substances: benzene, naphthalene, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, celestine, perylene, fluoranthene, benzo[a]fluoranthene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylenexide, terphenyl, diphenylenexide, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorene, cis or trans monobenzo[a]indo[a]fluorene, cis or trans dibenzo[a]indo[a]fluorene, trimer indo[a]fluorene, iso[a]fluorene, etc. Trimeric indene, spirotrimeric indene, spiroisotrimeric indene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indole-carbazole, indole-carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiamidazole, phenanthrenemidazole, pyridinium-imidazolium, quinoxaline-imidazolium, β-azole, benzo[β-azole], naphtho[β-azole], anthraxo[β-azole], phenanthrene[β-azole], iso[β-azole], 1,2-thiazole, 1,3-thiazole, benzo[β-thiazole], pyridazine, benzo[β-pyridazine], pyrimidine, benzo[β-pyrimidine], quinoxaline, 1,5-diazathane, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenothiazine, fluorescein ring, naphthidine, azacarbazole, benzo[β-carbline], phenanthrene, 1,2,3- Triazoles, 1,2,4-triazoles, benzotriazoles, 1,2,3-diazoles, 1,2,4-diazoles, 1,2,5-diazoles, 1,3,4-diazoles, 1,2,3-thiadiazoles, 1,2,4-thiadiazoles, 1,2,5-thiadiazoles, 1,3,4-thiadiazoles, 1,3,5-triazines, 1,2,4-triazines, 1,2,3-triazines, tetrazolium, 1,2,4,5-tetraazines, 1,2,3,4-tetraazines, 1,2,3,5-tetraazines, purines, pteridines, indoleazines, and benzothiadiazoles.

[0026] The abbreviation Ar in each case independently refers to: an aromatic or heteroaromatic ring system having 5 to 40 ring atoms and being substituted with one or more R' groups; or a heteroaromatic ring system having 5 to 24 ring atoms and being substituted with one or more R' groups, wherein details regarding the aromatic or heteroaromatic ring system also apply accordingly. The one or more R' groups have the definitions described above or below. The abbreviation Ar in each case preferably independently refers to: an aryl group having 6 to 40 ring atoms and being substituted with one or more R' groups; or a heteroaromatic group having 5 to 40 ring atoms and containing O or S as heteroatoms, said group being substituted with one or more R' groups, wherein details regarding the aryl group or heteroaromatic group and R' as described above or below also apply accordingly.

[0027] abbreviation Ar 11 Ar 12 Ar 21 and Ar 22 In each case, they may be the same or different and are: having 5 to 40 ring atoms and being able to be one or more R 3 Aromatic or heteroaromatic ring systems with substituent groups, wherein R 3 Group or substituent R 3 It has the definition as described above or below. Preferably, Ar 11 Ar 12 Ar 21 and Ar 22 In each case, they may be the same or different and are aryl groups having 6 to 40 ring atoms as described above.

[0028] In the context of this invention, cyclic alkyl, alkoxy, or thioalkyl groups should be understood to refer to monocyclic, bicyclic, or polycyclic groups.

[0029] In the context of this invention, straight-chain alkyl groups having 1 to 40 carbon atoms, and branched or cyclic alkyl groups having 3 to 40 carbon atoms, should be understood to refer to, for example: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl 1-Methylcyclopentyl, 2-Methylpentyl, n-Heptyl, 2-Heptyl, 3-Heptyl, 4-Heptyl, Cyclohepyl, 1-Methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1-Bicyclo[2.2.2]Octyl, 2-Bicyclo[2.2.2]Octyl, 2-(2,6-Dimethyl)Octyl, 3-(3,7-Dimethyl)Octyl, Adamantyl, Trifluoromethyl, Pentafluoroethyl, 2,2,2-Trifluoroethyl, 1,1-Dimethyl-n-hexyl-1- 1,1-Dimethyl-n-hept-1-yl, 1,1-Dimethyl-n-oct-1-yl, 1,1-Dimethyl-n-dec-1-yl, 1,1-Dimethyl-n-dodecane-1-yl, 1,1-Dimethyl-n-tetradecane-1-yl, 1,1-Dimethyl-n-hexadecane-1-yl, 1,1-Dimethyl-n-octadecane-1-yl, 1,1-Diethyl-n-hexane-1-yl, 1,1-Diethyl-n-heptane-1-yl, 1,1-Diethyl-n-octane-1-yl - 1,1-diethyl-n-decyl-1-yl, 1,1-diethyl-n-dodecyl-1-yl, 1,1-diethyl-n-tetradecyl-1-yl, 1,1-diethyl-n-hexadecyl-1-yl, 1,1-diethyl-n-octadecyl-1-yl, 1-(n-propyl)cyclohexyl-1-yl, 1-(n-butyl)cyclohexyl-1-yl, 1-(n-hexyl)cyclohexyl-1-yl, 1-(n-octyl)cyclohexyl-1-yl and 1-(n-decyl)cyclohexyl-1-yl groups.

[0030] A straight-chain alkoxy group having 1 to 40 carbon atoms or a branched alkoxy group having 3 to 40 carbon atoms shall be understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, or 2-methylbutoxy.

[0031] A straight-chain thioalkyl group having 1 to 40 carbon atoms should be understood to mean, for example, a thioalkyl group such as thiomethyl, 1-thioethyl, 1-thioisopropyl, 1-thion-propyl, 1-thioisobutyl, 1-thion-butyl or 1-thiotert-butyl.

[0032] An aryloxy or heteroaryloxy group having 5 to 60 ring atoms refers to an O-aryl or O-heteroaryl group, and refers to the aryl or heteroaryl group being bonded via an oxygen atom, wherein the aryl or heteroaryl group is defined as described above.

[0033] An aryl or heteroaryl group having 5 to 40 ring atoms refers to an alkyl group as described above that has been replaced by an aryl or heteroaryl group, wherein the aryl or heteroaryl group is defined as described above.

[0034] In the context of this specification, the phrase "two or more groups together can form a ring" should be understood to mean, in particular, that the two groups are connected to each other by chemical bonds. This will be illustrated by the following scheme: .

[0035] However, the above wording should also be understood to mean that if one of the two groups is hydrogen, the second group bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This will be illustrated by the following scheme: .

[0036] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 11 and Ar 12 They do not form monocyclic or polycyclic aliphatic or aromatic ring systems together.

[0037] In one embodiment of a compound represented by one of formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of formulas 1-1 to 1-3, the compound is represented by one of formulas 1-1-1 to 1-3-2:

[0038] Among them, in equations 1-1-1 to 1-3-2, X 11 To X 17 L 1 L 2 k1, k2, R 2 Ar 11 Ar 12 Ar 21 Ar 22 E has the definition given above or below.

[0039] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, L 1 and L 2 Each case is independently a single bond; or

[0040] Benzene, naphthalene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, spirodifluorene, anthracene, phenanthrene, pyrene, dihydropyrene, succinate, perylene, fluoranthene, benzo[a]anthracene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, iso[a] Quinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthridine, pyrazole, indazole, imidazole, benzimidazole, benzimidazole [1,2-a]benzimidazole, naphthiazole, phenanthridine, pyridinium pyridinium, quinoxaline imidazole, pyrazole, benzo[a]pyridine, naphthiazole, anthraquinone, phenanthridine, iso[a]pyridine 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthidine, azacarbazole, benzocarbline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-diazole, 1,2,4-diazole, 1,2,5-diazole, 1,3,4-diazole, 1, 2,3-Thiadiazole, 1,2,4-Thiadiazole, 1,2,5-Thiadiazole, 1,3,4-Thiadiazole, 1,3,5-Triazine, 1,2,4-Triazine, 1,2,3-Triazine, Tetrazolium, 1,2,4,5-Tetraazine, 1,2,3,4-Tetraazine, 1,2,3,5-Tetraazine, Purine, Pteridine, Indoleazine, or benzothiadiazole, the above substances may be converted by one or more R groups 3 Replace; R 3 It has the definition given above or below.

[0041] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, L 1 and L 2 In each case, it is independently a single bond; or benzene, naphthalene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, spirodifluorene, phenanthrene, dibenzofuran, dibenzothiophene, or carbazole, wherein the group may be R or one or more of the groups R 3 Replace; R 3 It has the definition given above or below.

[0042] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, L 1 and L 2 Each is a single bond independently in each case; or by formula Ar L -1 to Ar L One representation of -96:

[0043] In Ar L -1 to Ar L -96 in, The dashed lines connect to the corresponding remaining parts of each of equations 1-1 to 1-3; Various Ar L -1 to Ar L -96 can be R 3 The substitution is preferred, and preferably, H is only present in the positions shown as unsubstituted, or H is partially or completely replaced by D in the positions shown as unsubstituted. R 3 It has the definition given above or below; Wherein group R 3 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; and R 5 It has the definition given above or below.

[0044] In one embodiment of a compound represented by one of formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of formulas 1-1 to 1-3, the compound satisfies at least one of conditions 2-1 to 2-4: <Condition 2-1> k1 is 1 and L 1 It is a single key. <Condition 2-2> k2 is 1 and L 2 It is a single key. <Condition 2-3> k1 is 1 and L 1 Not a single key, <Condition 2-4> k2 is 1 and L 2 Not a single key.

[0045] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, X 11 To X 17 Not N.

[0046] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 11 To R 17 At least one of them is a group represented by formula 2-2.

[0047] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, X 13 For C(R) 13 And R 13 X is a group represented by formula 2-2. Preferably, in formula 1-3, X 13 For C(R) 13 And R 13 The group is represented by formula 2-2.

[0048] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 11 and Ar 12 Each occurrence is selected, either identically or differently, from monovalent groups derived from the following substances: benzene, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, dibenzothiophene, benzo[a]carbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, each group being enclosed by the group R. 3 Replace; and R 3 It has the definition given above or below.

[0049] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 11 and Ar12 Each occurrence is selected, either identically or differently, from monovalent groups derived from the following substances: benzene, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, dibenzofuran, benzo[a]furan, and benzo[a]thiophene, each group being marked with the group R. 3 Replace; and R 3 It has the definition given above or below.

[0050] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 11 and Ar 12 Each time it appears, the groups are selected from the following formula, either the same or different:

[0051] The dashed lines represent bonds connected to nitrogen atoms, and the groups shown at unsubstituted positions can be R 3 Group substitution, preferably having only H at the position shown as unsubstituted, or partially or completely replacing H with D at the position shown as unsubstituted.

[0052] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 11 and Ar 12 Same or different.

[0053] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 21 and Ar 22 Each occurrence is identical or different from a monovalent group derived from the following substances: benzene, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, dibenzothiophene, benzo[a]carbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, each group being enclosed by the group R. 3 Replace; and R 3 It has the definition given above or below.

[0054] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 21 and Ar 22 Each occurrence is selected, either identically or differently, from monovalent groups derived from the following substances: benzene, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, dibenzofuran, each group being enclosed by the group R. 3 Replace; and R 3 It has the definition given above or below.

[0055] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, Ar 21 and Ar 12 same.

[0056] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, the group represented by Formula 2-2 is represented by Formula 2-2-A:

[0057] In equation 2-2-A, R 31 To R 38 In each case, it refers independently to R. 3 The definition; and L 2 k2 and It has the definition given above or below.

[0058] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, wherein the compound represented by one of Formulas 1-1 to 1-3 comprises at least one deuterium.

[0059] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, (i) R 11 To R 17 At least one of them contains at least one deuterium; (ii) R a Contains at least one deuterium; (iii) R b (iv) The group represented by Formula 2-1 contains at least one deuterium; or (v) The group represented by Formula 2-2 contains at least one deuterium.

[0060] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, (i) R 11 To R 17 At least one of them is deuterium; (ii) R a Contains at least one deuterium; (iii) L 1 R in 3 At least one of them is deuterium; (iv) L 2 R in 3 At least one of them is deuterium; (v) Ar 11 and Ar 12 R in 3 At least one of them is deuterium; or (ⅵ) Ar 21 and Ar 22 R in 3 At least one of them is deuterium.

[0061] In one embodiment of the compound or in a preferred embodiment of the main material of the compound, R in formula (1) 11 To R 20 At least one of them contains at least one deuterium, wherein R 11 To R 20 At least one of them is via a linker -(L n ) na - 'With indolcarbazole moiety Z i or N-heteroaryl moiety Z h The binding site of the connection.

[0062] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 11 To R 17 In each case, they are independently H and D, and each can be generated by one or more groups R. 4 The substituted alkyl group is a straight-chain alkyl group having 1 to 40 carbon atoms or a branched alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 4 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, or groups represented by formula 2-2, wherein group R 11 To R 17 The two groups that can form can be formed by one or more groups R 4 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; and R 4 It has the definition given above or below.

[0063] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 11 To R 17 Each time it appears, it represents H, D, a straight-chain alkyl group having 1 to 40 C atoms or a branched alkyl group having 3 to 40 C atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or a group represented by Formula 2-2.

[0064] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 2 In each case, they are independently H, D, F, Cl, Br, I, CHO, CN, N(R)5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 3, B(OR) 5 )2, OSO2R 5 Each can be generated by one or more groups R 5 The substituted linear alkyl group having 1 to 40 carbon atoms or the branched or cyclic alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitution is performed, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or in each case by one or more R groups. 5 Substituted aromatic ring systems having 5 to 60 ring atoms, wherein the group R 2 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; and R 5 It has the definition given above or below.

[0065] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 2 In each case, each can be independently represented by one or more groups R. 5 The substituted linear alkyl group having 1 to 40 carbon atoms or the branched or cyclic alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5The substitution is performed, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or in each case by one or more R groups. 5 Substituted aromatic ring systems having 5 to 60 ring atoms, wherein the group R 2 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems.

[0066] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 3 In each case, they are independently H and D, and each can be generated by one or more groups R. 5 The substituted linear alkyl group having 1 to 40 carbon atoms or the branched or cyclic alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitution is performed, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or in each case by one or more R groups. 5 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, wherein the group R 2 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; and R 5 It has the definition given above or below.

[0067] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 3 Each occurrence may represent H or D in the same or different ways, or each may be represented by one or more groups R. 5 The substituted alkyl group is a straight-chain alkyl group having 1 to 40 carbon atoms or a branched alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; and R 5It has the definition given above or below.

[0068] In one embodiment of a compound represented by one of Formulas 1-1 to 1-3, or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by one of Formulas 1-1 to 1-3, R 11 To R 17 and R 2 To R 5 Each time Ar appears, it is selected from groups of formulas R-1 to R-187, either identically or differently, and each time Ar appears, it is selected from groups of formulas R-1 to R-139, either identically or differently:

[0069] The following compounds are examples of compounds represented by one of formulas 1-1 to 1-3:

[0070] Therefore, this application provides a method for preparing compounds according to this application, characterized in that: 1) F-Cl-fluorene is constructed by a Suzuki coupling reaction of a suitable benzoate with a substituted or unsubstituted phenylboronic acid, followed by a Grignard reaction and a ring-closing reaction; 2) carbazole is introduced by nucleophilic substitution at the F position; 3) a secondary amine is introduced by a Buchwald reaction; or 4) in the case of an aryl linker, an amine having a linker is introduced by a Suzuki reaction.

[0071] In one embodiment, a method for preparing a compound represented by one of formulas 1-1 to 1-3 is characterized in that the fluorenyl compound having at least one reactive group undergoes any of the following reactions: a) a reaction with a secondary amine in a Buchwald reaction, or b) a reaction with a boronic acid-substituted tertiary amine in a Suzuki reaction, or c) a reaction in sequence of i) a Suzuki reaction with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound, followed by ii) a Buchwald reaction of the resulting intermediate with a secondary amine.

[0072] By following these steps, and if necessary, by purification, such as recrystallization or sublimation, it is possible to obtain products with high purity, preferably above 99.9% (through...). 1 The purity (determined by ¹H NMR and / or HPLC) is used to obtain a compound represented by one of formulas 1-1 to 1-3.

[0073] For processing the compounds of the present invention from a liquid state, for example by spin coating or printing, formulations of the compounds of the present invention are required. These formulations may be, for example, solutions, dispersions, or emulsions. For this purpose, mixtures of two or more solvents are preferred. Suitable and preferred solvents are, for example: toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthylene, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, dimethylbenzene, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, styrene. Ketones, α-terpineol, benzothiazole, butyl benzoate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0074] The present invention similarly provides a formulation, particularly a solution, dispersion, or emulsion, comprising at least one compound of the present invention as described above, or a mixture of the present invention as described above, and at least one solvent, preferably an organic solvent. Methods for preparing such solutions are known to those skilled in the art.

[0075] Compounds represented by one of Formulas 1-1 to 1-3 are suitable for use in electronic devices, particularly organic light-emitting diodes (OLEDs). Depending on the substitution, compounds represented by one of Formulas 1-1 to 1-3 can be used for different functions and layers. They are preferably used as hole-transporting materials in hole-transporting layers and / or as matrix materials in light-emitting layers, and more preferably in combination with phosphorescent emitters.

[0076] Therefore, the present invention also provides the use of a compound represented by one of formulas 1-1 to 1-3 in an electronic device. The electronic device is preferably selected from: organic integrated circuits (OIC), organic field-effect transistors (OFET), organic thin-film transistors (OTFT), organic light-emitting transistors (OLET), organic solar cells (OSC), organic optical detectors, organic photosensors, organic field quenching devices (OFQD), organic light-emitting electrochemical cells (OLEC), organic laser diodes (O-lasers), and more preferably organic electroluminescent devices (OLED).

[0077] The present invention also provides an electronic device comprising at least one compound represented by one of formulas 1-1 to 1-3. The electronic device is preferably selected from the above-described devices.

[0078] Particularly preferred are organic electroluminescent devices comprising an anode, a cathode, and at least one light-emitting layer, characterized in that the device contains at least one organic layer comprising at least one compound represented by one of formulas 1-1 to 1-3. Preferably, an organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer is characterized in that at least one organic layer selected from the hole-transporting layer and the light-emitting layer comprises at least one compound represented by one of formulas 1-1 to 1-3.

[0079] The hole transport layer should be understood herein as all layers disposed between the anode and the light-emitting layer, preferably a hole injection layer, a hole transport layer, and an electron blocking layer. The hole injection layer should be understood herein as the layer directly adjacent to the anode. The hole transport layer should be understood herein as the layer between the anode and the light-emitting layer but not directly adjacent to the anode, and preferably not directly adjacent to the light-emitting layer either. The electron blocking layer should be understood herein as the layer between the anode and the light-emitting layer and directly adjacent to the light-emitting layer. The electron blocking layer preferably has a high-energy LUMO, thus preventing electrons from leaving the light-emitting layer.

[0080] In addition to the cathode, anode, and light-emitting layer, electronic devices may also include other layers. These are selected from, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers, charge generation layers, and / or organic or inorganic p / n junctions in each case. However, it should be noted that not every one of these layers is necessarily present, and the choice of layers always depends on the compound used, and especially on whether the device is a fluorescent electroluminescent device or a phosphorescent electroluminescent device.

[0081] The preferred order of layers in electronic devices is as follows: -anode- -Hollow Injection Layer- -Hole transport layer- -Optional additional hole transport layer- -Emitting Layer- -Optional hole-blocking layer- -Electron transport layer- -Electron Injection Layer- -cathode-.

[0082] At the same time, it should be pointed out again that not all of the mentioned layers necessarily exist and / or other layers may exist.

[0083] The organic electroluminescent device of the present invention may contain two or more emitting layers. More preferably, these emitting layers generally have multiple luminescence maximum values ​​between 380 nm and 750 nm, resulting in overall white light emission; in other words, a variety of luminescent compounds that can fluoresce or phosphore and emit blue, green, yellow, orange, or red light are used in the emitting layers. A three-layer system is particularly preferred, i.e., a system having three emitting layers, wherein in each case one of the three layers exhibits blue light emission, in each case one of the three layers exhibits green light emission, and in each case one of the three layers exhibits orange or red light emission. The compounds of the present invention are preferably present in the hole transport layer or in the emitting layers. It should be noted that, in order to produce white light, it may also be suitable to use a single luminescent compound that emits light over a wide wavelength range, rather than a variety of luminescent compounds that emit multiple colors.

[0084] Preferably, a compound represented by one of formulas 1-1 to 1-3 is used as the hole transport material. The luminescent layer may be a fluorescent luminescent layer or a phosphorescent luminescent layer. The luminescent layer is preferably a blue fluorescent layer or a green phosphorescent layer.

[0085] When a device containing a compound represented by one of Formulas 1-1 to 1-3 contains a phosphorescent emitting layer, the layer preferably contains two or more, preferably exactly two, different matrix materials (a mixed matrix system). Preferred embodiments of the mixed matrix system are described in further detail below.

[0086] If a compound represented by one of Formulas 1-1 to 1-3 is used as a hole transport material in a hole transport layer, a hole injection layer, or an electron blocking layer, the compound may be used as a pure material, i.e., in a 100% proportion in the hole transport layer, or it may be used in combination with one or more other compounds.

[0087] In a preferred embodiment, the hole-transporting layer comprising a compound represented by one of Formulas 1-1 to 1-3 further comprises one or more additional hole-transporting compounds. These additional hole-transporting compounds are preferably selected from triarylamine compounds, more preferably from monotriarylamine compounds. They are most preferably selected from preferred embodiments of the hole-transporting materials further specified below. In the preferred embodiment, the compound represented by one of Formulas 1-1 to 1-3 and one or more additional hole-transporting compounds are preferably present in a proportion of at least 10%, more preferably in a proportion of at least 20%.

[0088] In a preferred embodiment, the hole-transporting layer comprising a compound represented by one of formulas 1-1 to 1-3 further contains one or more p-type dopants. The p-type dopants used according to the invention are preferably those organic electron acceptor compounds capable of oxidizing one or more other compounds in the mixture.

[0089] Particularly preferred p-type dopants include: quinone dimethane compounds; azidofluorene dione; azidobenzonaphthalene; azidotriphenylide; I₂; metal halides, preferably transition metal halides; metal oxides, preferably metal oxides containing at least one transition metal or a metal from Group 3; and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a binding site. The dopants are also preferably transition metal oxides, preferably oxides of rhenium, molybdenum, and tungsten, more preferably Re₂O₇, MoO₃, WO₃, and ReO₃. Furthermore, bismuth complexes in the (III) oxidation state are preferred, especially bismuth (III) complexes with electron-deficient ligands, and even more particularly bismuth (III) complexes with carboxylic acid anion ligands.

[0090] The p-type dopant is preferably distributed substantially uniformly in the p-type doped layer. This can be achieved, for example, by co-evaporation of the p-type dopant and the hole transport material matrix. The p-type dopant is preferably present in the p-type doped layer at a ratio of 1% to 10%.

[0091] Preferred p-type dopants include, in particular, the following compounds:

[0092] In a preferred embodiment, a hole injection layer is present in the device if it conforms to one of the following embodiments: a) the hole injection layer comprises a triarylamine and a p-type dopant; or b) the hole injection layer comprises a single electron-deficient material (electron acceptor). In a preferred embodiment of embodiment a), the triarylamine is a monotriarylamine, particularly one of the preferred triarylamine derivatives further mentioned below. In a preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylide derivative as described in US 2007 / 0092755.

[0093] The compound represented by one of Formulas 1-1 to 1-3 may be present in the hole injection layer, hole transport layer, and / or electron blocking layer of the device. When the compound is present in the hole injection layer or hole transport layer, the compound is preferably p-type doped, meaning that the compound is in a form mixed with the p-type dopant as described above in the layer.

[0094] A compound represented by one of formulas 1-1 to 1-3 is preferably present in the electron blocking layer. In this case, the compound is preferably not p-type doped. More preferably, in this case, the compound is preferably a single compound in the layer without the addition of other compounds.

[0095] In an alternative preferred embodiment, a compound represented by one of formulas 1-1 to 1-3 is used as a matrix material in combination with one or more luminescent compounds, preferably phosphorescent compounds, in the luminescent layer. The phosphorescent compounds used here are preferably selected from red and green phosphorescent compounds.

[0096] In this case, the proportion of matrix material in the light-emitting layer is between 50.0 vol% and 99.9 vol%, preferably between 80.0 vol% and 99.5 vol%, and more preferably between 85.0 vol% and 97.0 vol%.

[0097] Accordingly, the proportion of the luminescent compound is between 0.1 vol% and 50.0 vol%, preferably between 0.5 vol% and 20.0 vol%, and more preferably between 3.0 vol% and 15.0 vol%.

[0098] The luminescent layer of an organic electroluminescent device may also comprise a system containing multiple matrix materials (a mixed matrix system) and / or multiple luminescent compounds. In this case, the luminescent compounds are typically those compounds present in a smaller proportion of the system, while the matrix materials are those compounds present in a larger proportion. However, in some cases, the proportion of a single matrix material in the system may be less than the proportion of a single luminescent compound.

[0099] Preferably, a compound represented by one of Formulas 1-1 to 1-3 is used as a component of the mixed matrix system, and more preferably as a component of the mixed matrix system for phosphorescent emitters. The mixed matrix system preferably comprises two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material with hole transport properties, and the other is a material with electron transport properties. It is also preferred that one of the materials is a compound with a large energy difference between HOMO and LUMO (wide bandgap material). The compound represented by one of Formulas 1-1 to 1-3 in the mixed matrix system is preferably a matrix material with hole transport properties. Accordingly, when a compound represented by one of Formulas 1-1 to 1-3 is used as the matrix material for a phosphorescent emitter in the light-emitting layer of an OLED, a second matrix compound with electron transport properties is present in the light-emitting layer. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1.

[0100] However, the desired electron transport and hole transport properties of the mixed matrix components can also be primarily or entirely incorporated into a single mixed matrix component, in which case one or more other mixed matrix components achieve other functions.

[0101] Preferably, the following material categories are used in the above-mentioned layers of the device: Phosphorescent light source: The term "phosphorescent luminescent material" generally includes compounds that emit light through spin-forbidden transitions, such as from an excited triplet state or from a state with a higher spin quantum number, such as a quintet state.

[0102] Suitable phosphorescent emitters are, in particular, compounds that emit light when properly excited, preferably in the visible light region; and further contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80. As phosphorescent emitters, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred, especially compounds containing iridium, platinum, or copper.

[0103] In the context of this invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent compounds.

[0104] Generally, all phosphorescent complexes known to those skilled in the art to be used in phosphorescent OLEDs and organic electroluminescent devices are suitable for use in the devices of this invention. Further examples of suitable phosphorescent emitters are shown in the table below:

[0105] Fluorescent light source: Preferred fluorescent compounds are selected from arylamines. In the context of this invention, arylamines or aromatic amines should be understood as compounds comprising three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracene diamines, aromatic pyreneamines, aromatic pyrene diamines, aromatic pyrimethamines, or aromatic pyrimethamines. Aromatic anthraceneamines should be understood as compounds in which a diaryl amino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracene diamines should be understood as compounds in which two diaryl amino groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Aromatic pyreneamines, pyrene diamines, pyrimethamines, and pyrimethamines are similarly defined, wherein the diaryl amino groups are preferably bonded to pyrene at the 1- or 1,6-positions. Also preferred luminescent compounds are indene-fluoreneamine or indene-fluorene diamine, benzo[a]indene-fluoreneamine or benzo[a]indene-fluorene diamine, and dibenzo[a]indene-fluoreneamine or dibenzo[a]indene-fluorene diamine, as well as indene-fluorene derivatives having fused aryl groups. Pyrene arylamines are also preferred. Benzo[a]indene-fluoreneamine, benzo[a]fluoreneamine, extended benzo[a]indene, phenazine, and fluorene derivatives linked to furan or thiophene units are also preferred.

[0106] Matrix materials for phosphors: Preferred matrix materials for phosphors are selected from the following categories: oligomeric aromatic compounds (e.g., 2,2',7,7'-tetraphenylspirodifluorene), especially oligomeric aromatic compounds containing fused aromatic groups; oligomeric aromatic vinyl compounds; multi-legged metal complexes; hole-conducting compounds; electron-conducting compounds, especially ketones, phosphine oxides, and sulfoxides; transisomers; boric acid derivatives; or benzenexane. Particularly preferred matrix materials are selected from the following categories: oligomeric aromatic compounds comprising naphthalene, anthracene, benzenexane, and / or pyrene, or transisomers of these compounds; oligomeric aromatic vinyl compounds; ketones; phosphine oxides; and sulfoxides. Very particularly preferred matrix materials are selected from the following categories: oligomeric aromatic compounds comprising anthracene, benzenexane, benzo[a]phenanthrene, and / or pyrene, or transisomers of these compounds. In the context of this invention, oligomeric aromatic compounds should be considered as compounds in which at least three aryl or aromatic vinyl groups are bonded to each other.

[0107] Matrix materials for phosphorescent emitters: Preferred matrix materials for phosphorescent emitters, in addition to compounds represented by one of formulas 1-1 to 1-3, include the following substances: aromatic ketones, aromatic phosphine oxides, or aromatic sulfoxides or aromatic sulfones; triarylamines; carbazole derivatives such as CBP (N,N-dicarbazolylbiphenyl) or carbazole derivatives; indole-carbazole derivatives; indo-carbazole derivatives; azirazole derivatives; bipolar matrix materials; silanes; borazine or borate esters; triazine derivatives; zinc complexes; diazacyclopentane or tetrazacyclopentane derivatives; phosphonium-diazacyclopentane derivatives; bridged carbazole derivatives; biphenylide derivatives; or lactams.

[0108] Electron transport materials: Suitable electron transport materials are, for example, compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010 or other materials used in these layers according to the prior art.

[0109] The material used for the electron transport layer can be any material used as an electron transport material in the electron transport layer according to existing technology. Particularly suitable are aluminum complexes such as Alq3, zirconium complexes such as Zrq4, lithium complexes such as Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, diazole derivatives, aromatic ketones, lactams, boranes, phosphazacyclopentane derivatives, and phosphine oxide derivatives.

[0110] Preferred electron transport and electron injection materials are shown in the table below:

[0111] Hole transport materials: In addition to compounds represented by one of Formulas 1-1 to 1-3, other compounds preferably used in the hole transport layer of the OLED of the present invention are indene-fluoreneamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives having a fused aromatic system, monobenzo-indenefluoreneamine, dibenzo-indenefluoreneamine, spirodifluoreneamine, fluoreneamine, spirodibenzopyranamine, dihydroacridine derivatives, spirodibenzofuran and spirodibenzothiophene, phenanthrene diarylamine, spirotribenzocycloheptatrienolone, spirodifluorene having a m-phenylenediamine group, spirodiacridine, xanthondiarylamine, and 9,10-dihydroanthracene spirospirone having a diarylamino group. Preferred hole transport compounds are shown in the table below:

[0112] Preferred cathodes for electronic devices are metals with low work function, metal alloys comprising multiple metals, or multilayer structures, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys composed of alkali metals or alkaline earth metals and silver, such as alloys composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, other metals with relatively high work function, such as Ag or Al, can be used. In this case, combinations of said metals are typically used, such as Ca / Ag, Mg / Ag, or Ba / Ag. It is also preferable to introduce a thin interlayer of material with a high dielectric constant between the metal cathode and the organic semiconductor. Examples of useful materials for this purpose are alkali metal fluorides or alkaline earth metal fluorides, and the corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.). Lithium quinoline (LiQ) can also be used for this purpose. The layer thickness is preferably between 0.5 nm and 5 nm.

[0113] The preferred anode is a material with a high work function. Preferably, the anode has a work function greater than 4.5 eV relative to vacuum. Firstly, for this purpose, metals with high redox potentials, such as Ag, Pt, or Au, are suitable. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also preferred. x Al / PtO xFor some applications, at least one of the electrodes must be transparent or partially transparent to allow for the illumination of organic materials (organic solar cells) or light emission (OLEDs, O-lasers). Preferred anode materials are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Conductive doped organic materials, especially conductive doped polymers, are also preferred. Furthermore, the anode may also consist of two or more layers, for example, an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide, or vanadium oxide.

[0114] In a preferred embodiment, the electronic device is characterized by coating one or more layers using a sublimation method. In this case, the material is sublimated in a vacuum sublimation system at a temperature of less than 10... -5 millibars, preferably less than 10 -6 An initial pressure of millibars is applied via vapor deposition. However, in this case, the initial pressure can also be even lower, for example, less than 10. -7 millibar.

[0115] Also preferred is an electronic device characterized by coating one or more layers using an OVPD (organic vapor deposition) method or by means of carrier gas sublimation. In this case, the material is in 10 -5 The material is applied at a pressure between millibar and 1 bar. A special case of this method is OVJP (Organic Vapor Jet Printing), in which the material is applied directly through a nozzle and thereby structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008). 92 (053301).

[0116] Another preferred electronic device is characterized by producing one or more layers from a solution, for example by spin coating, or by any printing method, such as screen printing, flexographic printing, nozzle printing, or offset printing, but more preferably by LITI (photoinitiated thermal imaging, thermal transfer) or inkjet printing. For this purpose, a soluble compound represented by one of formulas 1-1 to 1-3 is required. High solubility can be achieved through suitable substitution of the compound.

[0117] It is also preferred that the electronic device of the present invention is manufactured by applying one or more layers from a solution and by applying one or more layers by sublimation.

[0118] After applying the layer, the device is structured, contact connections are made, and finally sealed according to its application to prevent damage from water and air.

[0119] According to the present invention, electronic devices comprising one or more compounds represented by one of formulas 1-1 to 1-3 can be used in displays, as light sources in lighting applications, and as light sources in medical and / or cosmetic applications.

[0120] Example

[0121] A) Synthesis Examples

[0122] 1) Synthesis of Int-1a:

[0123] 35.9 g of methyl 3-bromo-2-fluoro-6-iodobenzoate (100 mmol), 19.4 g of phenylboronic acid (15 mmol), Pd(OAc)₂ (112 mg, 5 mol%), DPPF (338 mg, 6 mol%), and 22.5 g of K₃PO₄ (20 mmol) were dissolved in 400 mL of 1,2-dimethoxyethane. The reaction mixture was heated at 80 °C for 18 hours. The mixture was then cooled to room temperature. The reaction mixture was then concentrated on a rotary evaporator and purified by column chromatography (heptane / EtOAc) to obtain the desired product.

[0124] Yield: 20.5 g (66 mmol, 66%)

[0125] The following compounds can be synthesized in a similar manner:

[0126] 2) Synthesis of Int-2a

[0127] 20 g (65 mmol) of Int-1a was dissolved in 500 ml of dry THF and degassed. The solution was cooled to -78 °C and 174 ml (260 mmol) of methyllithium was added over a 40-minute period. The mixture was heated to -40 °C over a 1-hour period, and the reaction was monitored by TLC. When the reaction was complete, the mixture was carefully quenched with MeOH at -30 °C. The reaction solution was concentrated to one-third and 500 ml of dichloromethane was added. The solution was then washed, and the organic phase was dried over MgSO4 and evaporated.

[0128] Yield: 18.7 g (60.5 mmol, 93%)

[0129] The following compounds can be synthesized in a similar manner:

[0130] 3) Synthesis of Int-3a

[0131] 18 g (58.2 mmol) of Int-2a was dissolved in 1000 ml of degassed toluene, and a suspension of 40 g of polyphosphoric acid and 28 ml of methanesulfonic acid was added. The mixture was heated at 60 °C for 1 hour. The mixture was cooled and water was added. A solid precipitated and was dissolved in dichloromethane / THF (1:1). The solution was carefully alkalized with 20% NaOH, the phases were separated, and the organic phase was dried over MgSO4. The solid was washed with heptane by stirring. Yield: 15.4 g (53 mmol, 91%).

[0132] The following compounds can be synthesized in a similar manner:

[0133] 4) Synthesis of Int-4a

[0134] 60.5 g (0.22 mol) SM1.1, 37.3 g (0.22 mol) SM2.1, and 140.5 g (0.66 mol) potassium phosphate were dissolved in 1000 ml of dimethylformamide. The mixture was stirred at 120 °C for 18 hours until complete conversion. The mixture was concentrated under reduced pressure, and 1 L of water was added. The precipitate was filtered off and washed with water (2 × 500 ml), and stirred in 1000 ml of refluxed ethanol for 1 hour. The precipitate was filtered off, and the product as a solid was separated.

[0135] Yield: 79.3 g (0.199 mmol; 90%)

[0136] The following compounds can be synthesized in a similar manner:

[0137] 5) Synthesis of compound 1.1

[0138] 16.0 g (40.6 mmol) Int-1a, 24.8 g (44.7 mmol) SM3.1 and 16.8 g (121.9 mmol) potassium carbonate were dissolved in 500 ml dimethyl ether / toluene / water (2:2:1). 744 mg (0.81 mmol) Pd2(dba)3 and 1001 mg (2.4 mmol) S-Phos were added, and the mixture was refluxed for 18 hours. The mixture was cooled to room temperature, and 250 ml water and 250 ml toluene were added. The aqueous phase was extracted with toluene (2 × 200 ml), the combined organic phases were washed with water (2 × 200 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from ethanol by crystallization (toluene / heptane) and sublimation (10 -6 The product was obtained after further purification at 340°C.

[0139] Yield: 10.8 g (14.3 mmol, 36%)

[0140] The following compounds can be synthesized in a similar manner:

[0141] 6) Synthesis of compound 2.1

[0142] 12.52 g (31.78 mmol) Int-1a, 12.63 g (31.78 mmol) SM4.1 (897921-63-0), and 5.25 g (47.68 mmol) sodium tert-amyloxide were dissolved in 250 ml toluene. 291 mg (0.32 mmol) Pd2(dba)3 and 391 mg (0.95 mmol) 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl were added, and the mixture was refluxed for 3 hours. The mixture was cooled to room temperature, and 250 ml of water was added. The aqueous phase was extracted with toluene (2 × 200 ml), the combined organic phases were washed with water (2 × 200 ml), and dried over sodium sulfate. The solvent was reduced under reduced pressure. The residue was filtered through alumina (toluene). The crude product was further purified by crystallization (ethyl acetate / heptane; dimethyl ether / heptane), followed by sublimation (10 μL). -6 The product was obtained after (B)

[0143] Yield: 15.44 g (0.02 mol, 65%)

[0144] The following compounds can be synthesized in a similar manner:

[0145] B) Device Examples

[0146] 1) General manufacturing process and characterization of OLEDs

[0147] An OLED is applied to a glass substrate coated with a 50 nm thick structured ITO (indium tin oxide).

[0148] OLEDs generally have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emitting layer (EML) / electron transport layer, optionally with a second layer (ETL) / electron injection layer (EIL) and finally a cathode. The cathode is formed from a 100 nm thick aluminum layer. The exact structure of an OLED can be found in the table below. The materials used to manufacture OLEDs are shown in the table below.

[0149] All materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the luminescent layer consists of at least one matrix material (host material) and luminescent dopants added to one or more matrix materials by co-evaporation in a specific volume ratio. Details given in the form of H:SEB (95%:5%) refer to the fact that the volume ratio of material H present in the layer is 95% and the volume ratio of SEB is 5%.

[0150] Similarly, the electron transport layer and hole injection layer are also composed of a mixture of two materials. The structures of the materials used in OLEDs are shown in Table 3.

[0151] OLEDs were characterized using standard methods. For this purpose, electroluminescence spectra were measured; external quantum efficiency (EQE, in %) as a function of luminance was calculated from the current-voltage-luminance characteristics under assumed Lambertian radiation properties; and lifetime was determined. Parameter EQE @ 10 mA / cm² 2 This refers to 10 mA / cm 2 The external quantum efficiency obtained at U @ 10 mA / cm². 2 This refers to 10 mA / cm 2 The operating voltage is specified. Lifetime LT is defined as the time required for the brightness to decrease to a certain percentage under constant current density operation. The LT90 symbol indicates that the lifetime reported here corresponds to the time required for the brightness to decrease to 90% of its initial value. Symbol @ 80 mA / cm² 2Or @ 40 mA / cm 2 This refers to a lifetime of 80 mA / cm². 2 Below or at 40 mA / cm 2 The measurement was taken below.

[0152] 2) The EBL of the green phosphorescent OLED contains the compound of the present invention.

[0153] Manufacture the devices shown in the table below:

[0154] In the device setup shown above, the compounds of this invention exhibit very good efficiency and lifetime for phosphorescent green OLEDs:

[0155] 3) The EBL of the blue fluorescent OLED contains the compound of the present invention.

[0156] In the device setup shown above, the compounds of this invention exhibit very good efficiency and lifetime for fluorescent blue OLEDs:

[0157] The structures of the compounds used in the devices are shown in Table 3:

Claims

1. A compound, said compound being represented by one of formulas 1-1 to 1-3: The groups and markings that appear are as follows: X 11 For CR 11 Or N, X 12 For CR 12 Or N, X 13 For CR 13 Or N, X 14 For CR 14 Or N, X 15 For CR 15 Or N, X 16 For CR 16 Or N, and X 17 For CR 17 Or N; R a and R b Each occurrence represents a group represented by formula 2-1 or 2-2, and satisfies at least one of the following conditions 1-1 and 1-2: <Condition 1-1> R a Let R be the group represented by formula 2-1, and R b For the group represented by formula 2-2, <Condition 1-2> R a Let R be the group represented by formula 2-2, and R b The group represented by formula 2-1; L 1 and L 2 Each occurrence may represent a single key, either identically or differently, or each key may be represented by one or more R keys. 3 Aromatic or heteroaromatic ring systems with 5 to 40 ring atoms that are substituted with functional groups; k1 and k2 each time they appear, they may represent 1, 2, or 3, and where L 1 If it is a single bond, then k1 is 1, if L 2 If it is a single bond, then k2 is 1; Ar 11 Ar 12 Ar 21 and Ar 22 Each occurrence, whether identical or different, represents that each can be represented by one or more groups R. 3 Substituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms; E represents a single bond; R 11 To R 17 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) 4 )2,C(=O)R 4 , P(=O)(R 4 )2,S(=O)R 4 S(=O)2R 4 NO2, Si(R) 4 3, B(OR) 4 )2, OSO2R 4 Each can be generated by one or more groups R 4 The substituted linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or the branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 4 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms can be substituted by one or more R groups. 4 The substituted aryloxy group having 5 to 60 ring atoms, or the group represented by formula 2-2; wherein the group R 11 To R 18 The two groups that can form can be formed by one or more groups R 4 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; R 2 and R 3 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 3, B(OR) 5 )2, OSO2R 5 Each can be generated by one or more groups R 5 The substituted linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or the branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 5 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, or substituted aromatic or heteroaromatic ring systems that can be substituted by one or more R groups 5 Substituted aryloxy groups having 5 to 60 ring atoms; wherein group R 2 and R 3 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems; R 4 and R 5 Each occurrence may represent, in the same or different ways, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R', each of which is a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by R'C=CR', C≡C, ... Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O, S or CONR´ are substituted and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, in each case an aromatic or heteroaromatic ring system having 5 to 60 ring atoms that may be substituted by one or more groups R´, or an aryloxy group having 5 to 60 ring atoms that may be substituted by one or more groups R´, wherein two adjacent substituents R may form a monocyclic or polycyclic aliphatic or aromatic ring system that may be substituted by one or more groups R´; Ar, each time it appears, represents an aromatic or heteroaromatic ring system with 5 to 24 ring atoms that can be substituted by one or more groups R' in each case; R´, each time appearing, represents the same or different H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and one or more H atoms may be replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

2. The compound according to claim 1, wherein the compound is represented by one of formulas 1-1-1 to 1-3-2: Among them, in equations 1-1-1 to 1-3-2, X 11 To X 17 L 1 L 2 k1, k2, R 2 Ar 11 Ar 12 Ar 21 Ar 22 E has the definition given in claim 1.

3. The compound according to claim 1, L 1 and L 2 Each case is independent of the following: Single key; or Benzene, naphthalene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, spirodifluorene, anthracene, phenanthrene, pyrene, dihydropyrene, succinate, perylene, fluoranthene, benzo[a]anthracene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, iso[a] Quinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthridine, pyrazole, indazole, imidazole, benzimidazole, benzimidazole [1,2-a]benzimidazole, naphthiazole, phenanthridine, pyridinium pyridinium, quinoxaline imidazole, pyrazole, benzo[a]pyridine, naphthiazole, anthraquinone, phenanthridine, iso[a]pyridine 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthidine, azacarbazole, benzocarbline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-diazole, 1,2,4-diazole, 1,2,5-diazole, 1,3,4-diazole, 1, 2,3-Thiadiazole, 1,2,4-Thiadiazole, 1,2,5-Thiadiazole, 1,3,4-Thiadiazole, 1,3,5-Triazine, 1,2,4-Triazine, 1,2,3-Triazine, Tetrazolium, 1,2,4,5-Tetraazine, 1,2,3,4-Tetraazine, 1,2,3,5-Tetraazine, Purine, Pteridine, Indoleazine, or benzothiadiazole, the above substances may be converted by one or more R groups 3 replace.

4. The compound according to claim 1, wherein X 11 To X 17 Not N.

5. The compound according to claim 1, wherein R 11 To R 17 At least one of them is a group represented by formula 2-2.

6. The compound according to claim 1, wherein the group represented by formula 2-2 is represented by formula 2-2-A: In equation 2-2-A, R 31 To R 38 In each case, it refers independently to R. 3 The definition; and L 2 k2 and It has the definition given in claim 1.

7. The compound according to claim 1, wherein the compound represented by one of formulas 1-1 to 1-3 contains at least one deuterium.

8. The compound according to claim 1, wherein R 11 To R 17 In each case, they are independently H and D, and each can be generated by one or more groups R. 4 The substituted alkyl group is a straight-chain alkyl group having 1 to 40 carbon atoms or a branched alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The substitutions, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case by one or more R groups. 4 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, or groups represented by formula 2-2, wherein group R 11 To R 17 The two groups that can form can be formed by one or more groups R 4 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems.

9. The compound according to claim 1, wherein R 2 In each case, they are independently H, D, F, Cl, Br, I, CHO, CN, N(R) 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 3, B(OR) 5 )2, OSO2R 5 Each can be generated by one or more groups R 5 The substituted linear alkyl group having 1 to 40 carbon atoms or the branched or cyclic alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitution is performed, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or in each case by one or more R groups. 5 Substituted aromatic ring systems having 5 to 60 ring atoms, wherein the group R 2 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems.

10. The compound according to claim 1, wherein R 3 In each case, they are independently H and D, and each can be generated by one or more groups R. 5 The substituted linear alkyl group having 1 to 40 carbon atoms or the branched or cyclic alkyl group having 3 to 40 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The substitution is performed, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or in each case by one or more R groups. 5 Substituted aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, wherein the group R 2 The two groups that can form can be formed by one or more groups R 5 Substituted monocyclic or polycyclic aliphatic or aromatic ring systems.

11. A method for manufacturing a compound according to one or more of claims 1 to 10, comprising the following characteristics: A fluorenyl compound having at least one reactive group undergoes any of the following reactions: a) a reaction with a secondary amine in a Buchwald reaction, or b) a reaction with a boronic acid-substituted tertiary amine in a Suzuki reaction, or c) a reaction in sequence of i) a Suzuki reaction with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound, followed by ii) a Buchwald reaction in which the resulting intermediate reacts with a secondary amine, thereby yielding a compound according to one or more of formulas 1-1 to 1-3 as claimed in one to 10.

12. A formulation comprising at least one compound according to one or more of claims 1 to 10 and at least one solvent.

13. An electronic device comprising at least one compound according to one or more of claims 1 to 10.

14. The electronic device according to claim 13, characterized in that... The electronic device is an organic electroluminescent device and contains an anode, a cathode and at least one light-emitting layer, and is characterized in that the compound is contained in the hole transport layer or the light-emitting layer of the device.

15. Use of the compound according to one or more of claims 1 to 10 in an electronic device.

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